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Novel alkyd-type coating resins produced using cationic polymerization

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Abstract

Novel, partially bio-based poly(vinyl ether) copolymers derived from soybean oil and cyclohexyl vinyl ether (CHVE) were produced by cationic polymerization and investigated for application as alkyd-type surface coatings. Three different polymers were produced and cured clear coatings and free films characterized as a function of CHVE comonomer content and curing conditions. CHVE comonomer content was varied at 0, 25, and 50 wt%, and the three different curing conditions were 1 week at room temperature, 120°C for 1 h, and 150°C for 1 h. The results of the study showed that the thermal, mechanical, and physical properties of the coatings produced from these novel polymers varied considerably as a function of polymer composition and cure temperature. Overall, the results suggest a good potential for these novel copolymers to be used for coatings cured by autoxidation. Compared to conventional alkyd resins, which are produced by high temperature melt condensation polymerization, these poly(vinyl ether)s provide several advantages. These advantages include milder, more energy efficient polymer synthesis, elimination of issues associated with gelation during polymer synthesis, production of polymers with well-defined composition and relatively narrow molecular weight distribution, and elimination of film formation and physical property issues associated with entrained monomers, dimers, trimers, etc.

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References

  1. Perlack, RD, Wright, LL, Turhollow, AF, Graham, RL, Stokes, BJ, Erbach, DC, U.S. Department of Energy, Biomass as Feedstock for a Bioenergy and Bioproducts Industry: The Technical Feasibility of a Billion-Ton Annual Supply. Oak Ridge National Lab, Oak Ridge, TN, 2005

    Book  Google Scholar 

  2. Elliott, DC, “Chemicals from biomass.” Encycl. Energy, 1 163–174 (2004)

    Article  Google Scholar 

  3. Soucek, MD, Khattab, T, Wu, J, “Review of autoxidation and driers.” Prog. Org. Coat., 73 435–454 (2012)

    Article  Google Scholar 

  4. Muizebelt, WJ, Donkerbroek, JJ, Nielen, MWF, Hussem, JB, Biemond, MEF, Klaasen, RP, Zabel, KH, “Oxidative crosslinking of alkyd resins studied with mass spectrometry and NMR using model compounds.” J. Coat. Technol., 70 83–93 (1998)

    Article  Google Scholar 

  5. Falla, NAR, “Linoleic based coatings: a study of the dry film structure.” J. Coat. Technol., 64 55–60 (1992)

    Google Scholar 

  6. Mallegol, J, Gardette, JL, Lemaire, J, “Long-term behavior of oil-based varnishes and paints I. Spectroscopic analysis of curing drying oils.” J. Am. Oil Chem. Soc., 76 967–976 (1999)

    Article  Google Scholar 

  7. Mallegol, J, Gardette, JL, Lemaire, J, “Long-term behavior of oil-based varnishes and paints. Fate of hydroperoxides in drying oils.” J. Am. Oil Chem. Soc., 77 249–255 (2000)

    Article  Google Scholar 

  8. Hofland, A, “Alkyd resins: from down and out to alive and kicking.” Prog. Org. Coat., 73 274–282 (2012)

    Article  Google Scholar 

  9. Wicks, ZW, Jones, FN, Pappas, SP, Wicks, DA, Organic Coatings: Science and Technology. Wiley, Hoboken, NJ, 2007

    Book  Google Scholar 

  10. Chernykh, A, Alam, S, Jayasooriya, A, Bahr, J, Chisholm, BJ, “Living carbocationic polymerization of a vinyl ether monomer derived from soybean oil, 2-(vinyloxy)ethyl soyate.” Green Chem., 15 1834–1838 (2013)

    Article  Google Scholar 

  11. Alam, S, Kalita, H, Kudina, O, Popadyuk, A, Chisholm, BJ, Voronov, A, “Soy-based surface active copolymers as a safer replacement for low molecular weight surfactants.” ACS Sustain. Chem. Eng., 1 19–22 (2013)

    Google Scholar 

  12. Alam, S, Chisholm, BJ, “Coatings derived from novel, soybean oil-based polymers produced using carbocationic polymerization.” J. Coat. Technol. Res., 8 671–683 (2011)

    Article  Google Scholar 

  13. Alam, S, Kalita, H, Jayasooriya, A, Samanta, S, Bahr, J, Chernykh, A, Weiz, M, Chisholm, BJ, “2-(Vinyloxy)ethyl soyate as a versatile platform chemical for coatings: an overview.” Eur. J. Lipid Sci. Technol., 116 2–15 (2014)

    Article  Google Scholar 

  14. Popadyuk, A, Kalita, H, Chisholm, BJ, Voronov, A, “Evaluation of soy-based surface active copolymers as surfactant ingredients in model shampoo formulations.” Int. J. Cos. Sci., 36 537–545 (2014)

    Article  Google Scholar 

  15. Kalita, H, Selvakumar, S, Jayasooriyamu, A, Fernando, S, Samanta, S, Bahr, J, Alam, S, Sibi, M, Vold, J, Ulven, C, Chisholm, BJ, “Bio-based poly(vinyl ether)s and their application as alkyd-type surface coatings.” Green Chem., 16 1974–1986 (2014)

    Article  Google Scholar 

  16. Cramail, H, Deffieux, A, “Living cationic polymerization of cyclohexyl vinyl ether.” Macromol. Chem. Phys., 195 217–227 (1994)

    Article  Google Scholar 

  17. Aoshima, S, Kanaoka, S, “A renaissance in living cationic polymerization.” Chem. Rev., 109 5245–5287 (2009)

    Article  Google Scholar 

  18. Kanazawa, A, Kanaoka, S, Aoshima, S, “Major progress in catalysts for living cationic polymerization of isobutyl vinyl ether: effectiveness of a variety of conventional metal halides.” Macromolecules, 42 3965–3972 (2009)

    Article  Google Scholar 

  19. Aoshima, S, Higashimura, T, “Living cationic polymerization of vinyl monomers by organoaluminum halides. 3. Living polymerization of isobutyl vinyl ether by ethyldichloroaluminum in the presence of ester additives.” Macromolecules, 22 1009–1013 (1989)

    Article  Google Scholar 

  20. Oliveira, JS, Montalvao, R, Daher, L, Suarez, PAZ, Rubim, JC, “Determination of methyl ester contents in biodiesel blends by FTIR-ATR and FTNIR spectroscopies.” Talanta, 69 1278–1284 (2006)

    Article  Google Scholar 

  21. Siatis, NG, Kimbar, CS, Tarantilis, PA, Polissiou, MG, “Improvement of biodiesel production based on the application of ultrasound: monitoring of the procedure by FTIR spectroscopy.” J. Am. Oil Chem. Soc., 83 53–57 (2006)

    Article  Google Scholar 

  22. Fox, TG, “Influence of diluent and of copolymer composition on the glass transition temperature of a polymer system.” Bull. Am. Phys. Soc., 1 123–124 (1956)

    Google Scholar 

  23. Flory, PJ, Principles of Polymer Chemistry. Cornell University Press, Ithaca, NY, 1953

    Google Scholar 

  24. Murayama, T, Dynamic Mechanical Analysis of Polymeric Materials. Elsevier, Amsterdam, 1978

    Google Scholar 

  25. Hill, LW, “Structure/Property relationships of thermoset coatings.” J. Coat. Technol., 64 29–41 (1992)

    Google Scholar 

  26. Koleske, JV, “Mechanical properties of solid coatings.” Encyclopedia of Analytical Chemistry. Wiley, New York, 2006

    Google Scholar 

  27. Williams, ML, Landel, RF, Ferry, JD, “The temperature dependence of relaxation mechanisms in amorphous polymers and other glass-forming liquids.” J. Am. Chem. Soc., 77 3701–3707 (1955)

    Article  Google Scholar 

  28. Sperling, LH, “Basic viscoelastic definitions and concepts.” In: Corsaro, RD, Sperling, LH (eds.) 424th ACS Symposium Series, Sound and Vibration Damping with Polymers, 1990

Download references

Acknowledgment

The authors thank the United States Department of Agriculture/National Institute of Food Agriculture (Grant 2012-38202-19283), the Department of Energy (Grant DE-FG36-08GO88160), and the North Dakota Soybean Council for financial support.

Disclaimer

This report was prepared as an account of work sponsored by an agency of the United States Government. Neither the United States Government nor any agency thereof, nor any of their employees, makes any warranty, express or implied, or assumes any legal liability or responsibility for the accuracy, completeness, or usefulness of any information, apparatus, product, or process disclosed, or represents that its use would not infringe privately owned rights. Reference herein to any specific commercial product, process, or service by trade name, trademark, manufacturer, or otherwise does not necessarily constitute or imply its endorsement, recommendation, or favoring by the United States Government or any agency thereof. The views and opinions of authors expressed herein do not necessarily state or reflect those of the United States Government or any agency thereof.

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Authors and Affiliations

  1. Center for Nanoscale Science and Engineering, North Dakota State University, Fargo, ND, 58102, USA

    Harjyoti Kalita, Samim Alam, Anurad Jayasooriyamu, Shashi Fernando, Satyabrata Samanta, James Bahr & Bret J. Chisholm

  2. Department of Chemistry and Biochemistry, North Dakota State University, Fargo, ND, 58102, USA

    Sermadurai Selvakumar & Mukund Sibi

  3. Department of Mechanical Engineering, North Dakota State University, Fargo, ND, 58102, USA

    Jessica Vold & Chad Ulven

  4. Department of Coatings and Polymeric Materials, North Dakota State University, Fargo, ND, 58102, USA

    Deep Kalita & Bret J. Chisholm

  5. Materials and Nanotechnology Program, North Dakota State University, Fargo, ND, 58102, USA

    Bret J. Chisholm

Authors
  1. Harjyoti Kalita
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  2. Samim Alam
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  3. Deep Kalita
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  4. Anurad Jayasooriyamu
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  5. Shashi Fernando
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  6. Satyabrata Samanta
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  7. James Bahr
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  8. Sermadurai Selvakumar
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  9. Mukund Sibi
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  10. Jessica Vold
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  11. Chad Ulven
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  12. Bret J. Chisholm
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Correspondence to Bret J. Chisholm.

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Kalita, H., Alam, S., Kalita, D. et al. Novel alkyd-type coating resins produced using cationic polymerization. J Coat Technol Res 12, 633–646 (2015). https://doi.org/10.1007/s11998-015-9667-2

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  • DOI: https://doi.org/10.1007/s11998-015-9667-2

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